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Compound Detail

CHEMBL46469

ANTHRALIN
🧪 Phase II
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🧪 Phase II
O=C1c2c(O)cccc2Cc2cccc(O)c21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL46469
Name ANTHRALIN
Phase Phase II
Structure Type MOL
InChI Key NUZWLKWWNNJHPT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Alphodith Anthra-derm Anthraderm Anthralin Antraderm Batidrol Batridol Chrysodermol Cignolin Cigthranol Derobin Dithranol +17 more
11
Targets
41
Activities
3
Assay Types
0
PK Parameters
20
Publications
29
Known Names
1
Indications
1
Mechanisms

Molecular Properties

226.2
MW (Da)
2.23
ALogP
3
HBA
2
HBD
57.5
PSA (Ų)
0.62
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C14H10O3
MW 226.23
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness 0.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Psoriasis

ATC Classification

D05AC01
dithranol
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS
D05AC51
dithranol, combinations
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Activity Summary

IC50 37 meas. best 7.0
EC50 3 meas. best 4.78
Ki 1 meas. best 4.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NAD-dependent protein deacylase sirtuin-5, mitochondrial
CHEMBL2163183
 IC50 7.0 7.0 100.0 2
HaCaT
CHEMBL614392
 IC50 6.7 6.11 200.0 16
Serine protease hepsin
CHEMBL2079849
 IC50 6.64 6.64 230.0 1
Unchecked
CHEMBL612545
 IC50 6.22 5.0875 603.9 4
ADMET
CHEMBL612558
 IC50 6.16 6.16 700.0 3
Trypsin
CHEMBL2366
 IC50 5.9 5.9 1260.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 5.16 5.16 7000.0 1
Arachidonate 5-lipoxygenase
CHEMBL2980
 IC50 4.92 4.528 12000.0 5
Radical scavenging activity
CHEMBL613712
 EC50 4.78 4.78 16700.0 3
PMNL
CHEMBL613706
 IC50 4.43 4.43 37000.0 1
Unchecked
CHEMBL612545
 Ki 4.33 4.33 47000.0 1
Liposome
CHEMBL614676
 IC50 4.1 4.1 79000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NAD-dependent protein deacylase sirtuin-5, mitochondrial IC50 = 100.0 nM 7.0 Inhibition of SIRT5 (unknown origin) using GGQSLK[succ]FGKG as substrate after 3... 29494161
NAD-dependent protein deacylase sirtuin-5, mitochondrial IC50 = 100.0 nM 7.0 Inhibition of SIRT5 (unknown origin) 32858418
HaCaT IC50 = 200.0 nM 6.7 Antiproliferative activity against HaCaT cells 8201600
Serine protease hepsin IC50 = 230.0 nM 6.64 High-Throughput Screening Assay: To identify novel inhibitors of hepsin, the Che... -
HaCaT IC50 = 600.0 nM 6.22 Antiproliferative (inhibition of cell growth) activity against HaCaT cells (huma... 9371243
HaCaT IC50 = 600.0 nM 6.22 Antiproliferative activity (AA) against HaCaT keratinocytes. 9276024
Unchecked IC50 = 603.9 nM 6.22 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
ADMET IC50 = 700.0 nM 6.16 Antiproliferative activity against growth of HaCaT cell was determined 11140730
HaCaT IC50 = 700.0 nM 6.16 Antihyperproliferative activity against human HaCaT cells after 48 hrs by phase ... 26840368
HaCaT IC50 = 700.0 nM 6.16 Antiproliferative activity against human HaCaT cells 26515039
HaCaT IC50 = 700.0 nM 6.16 Antihyperproliferative activity against human HaCaT cells assessed as inhibition... 24964246
HaCaT IC50 = 700.0 nM 6.16 Antihyperproliferative activity against human HaCaT cells after 48 hrs by phase ... 22845014
HaCaT IC50 = 700.0 nM 6.16 Antiproliferative activity against human HaCaT cells assessed as dispersed cells... 20850910
HaCaT IC50 = 700.0 nM 6.16 Antiproliferative activity against human HaCaT cells after 48 hrs by phase contr... 20828887
HaCaT IC50 = 700.0 nM 6.16 Antiproliferative activity against human HaCaT cells after 48 hrs by phase contr... 20452101
HaCaT IC50 = 700.0 nM 6.16 Antiproliferative activity against human HaCaT cells 10395495
HaCaT IC50 = 700.0 nM 6.16 Antiproliferative activity against human HaCaT cells 10479319
ADMET IC50 = 700.0 nM 6.16 In vitro for antiproliferate activity against HaCaT cells 9873705
ADMET IC50 = 700.0 nM 6.16 Concentration required to inhibit 50% growth of HaCaT cells 11262091
HaCaT IC50 = 700.0 nM 6.16 Antihyperproliferative activity against human HaCaT cells after 48 hrs by MTT as... 28410493

Literature References

PubMed DOI Target Context # Activities
26515039 10.1016/j.bmc.2015.10.022 HaCaT 7
22944332 10.1016/j.bmc.2012.07.048 NON-PROTEIN TARGET 7
11140730 10.1016/s0960-894x(00)00599-0 ADMET 6
619147 10.1021/jm00199a005 No relevant target 6
15387642 10.1021/np049873n HaCaT 5
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 5
11262091 10.1021/jm001073w ADMET 5
22944332 10.1016/j.bmc.2012.07.048 HaCaT 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30351002 10.1021/acs.jmedchem.8b01363 Unchecked 4
26515039 10.1016/j.bmc.2015.10.022 No relevant target 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
20014752 10.1021/tx900326k Hepatotoxicity 3
8258834 10.1021/jm00077a015 Arachidonate 5-lipoxygenase 2
20828887 10.1016/j.ejmech.2010.08.047 HaCaT 2
9873705 10.1016/s0960-894x(98)00580-0 ADMET 2
9276024 10.1021/jm9701785 HaCaT 2
11262091 10.1021/jm001073w Unchecked 2
20452101 10.1016/j.ejmech.2010.04.013 HaCaT 2
22845014 10.1021/jm3009597 HaCaT 2

Data from ChEMBL 36 via Core Engine